Dimethylamine → 5-Dimethylaminomethyl-8-hydroxy-7-methoxyquinoline

HRID 280020Notes

Reaction equation

HRID 280020 reaction equation
[OH:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[CH3:14][NH:15][CH3:16].[CH2:17]=O>C(O)C>[CH3:14][N:15]([CH2:17][C:5]1[CH:4]=[C:3]([O:12][CH3:13])[C:2]([OH:1])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2)[CH3:16]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 128498147-Methoxyquinolin-8-ol

Product 1

HCID 201297875-Dimethylaminomethyl-8-hydroxy-7-methoxyquinolineYield 69.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a cold (0°) solution of 8-hydroxy-7-methoxyquinoline (0.92 g, 5.25 mmol) and 26% aqueous dimethylamine (3.0 g, 17 mmol) in 10 mL of ethanol was added dropwise 37% aqueous formaldehyde (0.77 g, 9.5 mmol). After stirring at room temperature for 1 hr, the mixture was refluxed for 30 min, cooled and evaporated to dryness. The residue was diluted with water, extracted with ether and dried (MgSO4). Evaporation gave 5-dimethylaminomethyl-8-hydroxy-7-methoxyquinoline as an oil (0.85 g, 69%); structure confirmed by NMR. This oil (0.85 g, 3.6 mmol) was heated under nitrogen with 2,4-diamino-6-methylthiopyrimidine (0.57 g, 3.6 mmol) in ethylene glycol (5 mL) at 140°-165° for 45 min, then cooled. The solid that separated was collected, and washed with ethanol and ether to give 2,4-diamino-5-(8-hydroxy-7-methoxy-5-quinolylmethyl)-6-methylthiopyrimidine as a tan solid (0.47 g, 37%), structure confirmed by NMR and mass spectroscopy. A portion of this solid (0.38 g, 1.1 mmol) was used in the procedure of Example 11B to give the title compound (mp 245°-250° dec). Anal. Calcd for C17H19N5SO2.0.5H2O: C, 55.72; H, 5.50; N, 19.11; S, 8.75. Found: C, 55.71; H, 5.51; N, 19.11; S, 8.74.

Workup

  1. temperaturethe mixture was refluxed for 30 min
  2. temperaturecooled
  3. customevaporated to dryness
  4. additionThe residue was diluted with water
  5. extractionextracted with ether
  6. dry with materialdried (MgSO4)
  7. customEvaporation

Sources & evidence

ORD record
ord-704dd15bf34d475e8958c78f3e81ed2d
Source dataset
uspto-grants-1986_05
Patent number
US04587342

Reaction notes

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